Bicyclic thioglycolate lactam

A method relying on the reduction of bicyclic thioglycolate lactams by lithium di-f-butylbiphenylide (LiDBB) has also been proposed (Scheme 48)196. This route has the advantage of affording carboxamide enolates with E/Z ratios that depend directly on the stereochemistry of the starting bicyclic lactam and do not rely on the steric difference between the two substituents. 

The chiral auxiliary method may be used for the synthesis of all-carbon quaternary stereocentresThus, chiral bicyclic thioglycolate lactam 1.50 is alkylated three times and... 

This reagent serves as a precursor to stereochemically defined, fully substituted amide enolates and so provides a method for stereoselective quaternary carbon formation. The two-electron reduction of a,a-dialkylated bicyclic thioglycolate lactams, prepared by sequential alkyaltion of lactam in THE with EDA... 

---

See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

---